EP0220518A2 - Préparation d'esters de 2,3-dicarboxylique-pyridines substitués et disubstitués - Google Patents

Préparation d'esters de 2,3-dicarboxylique-pyridines substitués et disubstitués Download PDF

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Publication number
EP0220518A2
EP0220518A2 EP86113409A EP86113409A EP0220518A2 EP 0220518 A2 EP0220518 A2 EP 0220518A2 EP 86113409 A EP86113409 A EP 86113409A EP 86113409 A EP86113409 A EP 86113409A EP 0220518 A2 EP0220518 A2 EP 0220518A2
Authority
EP
European Patent Office
Prior art keywords
substituted
preparation
formula
phenyl
diethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP86113409A
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German (de)
English (en)
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EP0220518A3 (en
EP0220518B1 (fr
Inventor
Robert F. Doehner, Jr.
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to AT86113409T priority Critical patent/ATE60758T1/de
Publication of EP0220518A2 publication Critical patent/EP0220518A2/fr
Publication of EP0220518A3 publication Critical patent/EP0220518A3/en
Application granted granted Critical
Publication of EP0220518B1 publication Critical patent/EP0220518B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3

Definitions

  • Literature methods for preparing 5,6-dialkyl and 5,6-alkyl-arylpyridine-2,3-dicarboxylates are limited, often requiring oxidation of alkyl or aryl substituents at positions 2 and 3 in order to obtain diacids.
  • R. Jones, J. Am. Chem. Soc. 73, 4380 (1951) describes a method in which reaction of a primary enamine yields 6-alkyl-pyridine 2,3-dicarboxylates which contain electron withdrawing substituents such as COCH 3 , CN or CO 2 Et in the 5-position.
  • Pyridine-2,3-dicarboxylates are useful intermediates for the preparation of herbicidal 2-(2-imidazolin-2-yl) nicotinic acids, esters and salts such as those disclosed in European Patent Application Number 81103638.3 filed December 1, 1981, as illustrated in Flow Diagram I below.
  • R is C,-C4 alkyl
  • R 2 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl
  • R, and R2 when R, and R2 are taken together with the carbon to which they are attached they may represent C 3 -C 6 cycloalkyl optionally substituted with methyl
  • W is 0 or S
  • R 3 and R 4 are hydrogen, halogen C 1 -C 6 straight or branched alkyl, alkenyl, or phenyl optionally substituted
  • R s and R 6 are each C 1 -C 4 alkyl.
  • the present invention is a novel method for the preparation of substituted and disubstituted pyridine 2,3-dicarboxylates of formula I wherein R 3 is hydrogen, halogen, C 1 -C 6 straight or branched alkyl, alkenyl, phenyl, or substituted-phenyl; R 4 and R 7 are each hydrogen, C 1 -C 6 straight or branched alkyl, alkenyl, phenyl, or substituted-phenyl; R 5 and R 6 are each C 1 -C 4 alkyl; comprising reacting an ⁇ -halo- ⁇ -ketoester of formula II wherein R 5 and R 6 are defined above and X is halogen preferably CI with an ⁇ , ⁇ -unsaturated aldehyde or ketone of formula III wherein R 3 , R4 and R 7 as described for in formula I above in the presence of a minimum of 2 molar equivalents of an ammonium salt in an organic solvent, in a temperature range of ambient temperature
  • Solvents suitable for use in the method of this invention include: water, alcohols, chlorinated hydrocarbons, hydrocarbons, aromatic hydrocarbons, ethers, organic acids, esters, and aprotic solvents such as acetonitrile.
  • pyridine-2,3-dicarboxylates containing substituents in the 4-, 5-and 6-position may conveniently be prepared by admixing essentially equimolar amounts of a formula II ⁇ -halo-ketoester and a formula III ⁇ , ⁇ -unsaturated aldehyde or ketone with a minimum of 2 molar equivalents of an ammonium salt in a suitable solvent, and stirring the resulting reaction mixture at a temperature in the range of ambient temperature to the boiling point of the solvent, and preferrably at reflux, until the reaction is essentially complete and isolating the thus-formed 4-substituted, 4,5-disubstituted, 5-substituted, 6-substituted or 5,6- disubstituted pyridine-2,3-dicarboxylate by standard laboratory techniques such as extraction, evaporation or column chromatography.
  • the method of the present invention is suitable for the preparation of substituted nicotiriates of formula IV below wherein R3, R 4 , R 6 and R, are as described for formula I; and R 8 is C 1 -C 4 alkyl; comprising reacting an a-halo- ⁇ -ketoester of formula V wherein R 6 and R 8 are as defined for formula IV above, with an ⁇ , ⁇ -unsaturated aldehyde or ketone of formula III.
  • Formula IV nicotinates are also useful intermediates for the preparation of herbicidal 2-(2-imidazolin-2-yl) nicotinic acids, esters and salts by reaction with an aminocarboxamide in the presence of at least 3 equivalents of sulfur as described in United States Patent 4,474,962 or by oxidation of R 8 , for example, by the procedure described in United States Patent 4,459,409, to yield the pyridine-2,3-dicarboxylic acid compounds of formula I above.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP86113409A 1985-10-28 1986-09-30 Préparation d'esters de 2,3-dicarboxylique-pyridines substitués et disubstitués Expired - Lifetime EP0220518B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT86113409T ATE60758T1 (de) 1985-10-28 1986-09-30 Herstellung von substituierten und disubstituierten estern von pyridin-2,3dicarbons|uren.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US791671 1985-10-28
US06/791,671 US4723011A (en) 1985-10-28 1985-10-28 Preparation of substituted and disubstituted-pyridine-2,3-dicarboxylate esters

Publications (3)

Publication Number Publication Date
EP0220518A2 true EP0220518A2 (fr) 1987-05-06
EP0220518A3 EP0220518A3 (en) 1988-03-30
EP0220518B1 EP0220518B1 (fr) 1991-02-06

Family

ID=25154435

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86113409A Expired - Lifetime EP0220518B1 (fr) 1985-10-28 1986-09-30 Préparation d'esters de 2,3-dicarboxylique-pyridines substitués et disubstitués

Country Status (18)

Country Link
US (1) US4723011A (fr)
EP (1) EP0220518B1 (fr)
JP (1) JPH0768216B2 (fr)
KR (1) KR940001774B1 (fr)
AR (1) AR241244A1 (fr)
AT (1) ATE60758T1 (fr)
AU (1) AU592379B2 (fr)
BR (1) BR8605210A (fr)
CA (1) CA1274831A (fr)
CS (1) CS259894B2 (fr)
DD (1) DD254000A5 (fr)
DE (1) DE3634975C2 (fr)
DK (1) DK163505C (fr)
ES (1) ES2000910A6 (fr)
HU (1) HU198909B (fr)
IE (1) IE59324B1 (fr)
IL (1) IL80284A (fr)
ZA (1) ZA868167B (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2595354A1 (fr) * 1986-03-10 1987-09-11 Shell Int Research Preparation de composes heterocycliques
EP0274379A2 (fr) * 1987-01-06 1988-07-13 Sugai Chemical Industry Co., Ltd. Procédé de préparation de dérivés d'acide pyridine-2,3-dicarboxylique
EP0357792A1 (fr) * 1988-03-18 1990-03-14 Sugai Chemical Industry Co., Ltd. Procede de preparation de composes de l'acide pyridine-2,3-dicarboxylique
EP0415767A2 (fr) * 1989-08-31 1991-03-06 Hoechst Celanese Corporation Procédé pour la préparation de dérivés d'acide pyridine-carboxylique
EP0461401A1 (fr) * 1990-06-15 1991-12-18 American Cyanamid Company Procédé pour la préparation des esters dialcoyliques 2,3-dicarboxy-pyridine et leurs dérivés à partir des esters dichloromaléiques
US5175300A (en) * 1988-03-18 1992-12-29 Sugai Chemical Ind. Co., Ltd. Process for preparing pyridine-2,3-dicarboxylic acid compounds
EP0564083A1 (fr) * 1992-03-30 1993-10-06 Hoechst Celanese Corporation Conversion d'esters d'acide pyridine-2,3-dicarboxyliques en leur anhydrides cycliques
DE102005022043B3 (de) * 2005-05-09 2006-09-28 MAE Maschinen- und Apparatebau Götzen GmbH & Co. KG Verfahren und Vorrichtung zum Richten eines länglichen Werkstückes
US8161289B2 (en) 2005-12-21 2012-04-17 SanDisk Technologies, Inc. Voice controlled portable memory storage device

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0625116B2 (ja) * 1987-07-08 1994-04-06 ダイソー株式会社 ピリジン−２，３−ジカルボン酸誘導体の製造法
US4871859A (en) * 1988-03-02 1989-10-03 Hoechst Celanese Corporation Process for preparing pyridine carboxylic acid esters
US5047542A (en) * 1988-07-01 1991-09-10 Hoechst Celanese Corporation Process for preparing pyridine carboxylic acid esters
WO1989008103A1 (fr) * 1988-03-02 1989-09-08 Hoechst Celanese Corporation Procede de preparation d'esters d'acide carboxylique de pyridine
DE3840554A1 (de) * 1988-12-01 1990-06-13 Wacker Chemie Gmbh Verfahren zur herstellung von pyridin-2,3-dicarbonsaeureestern
US4925944A (en) * 1989-03-21 1990-05-15 American Cyanamid Company Process for the preparation of o-carboxypyridyl- and o-carboxyquinolylimidazolinones
US5405987A (en) * 1989-08-31 1995-04-11 Hoechst Celanese Corporation Process for preparing pyridine and quinoline derivatives
US5322948A (en) * 1989-08-31 1994-06-21 Hoechst Celanese Corporation Process for preparing pyridinecarboxylic acid derivatives
US5118809A (en) * 1990-06-15 1992-06-02 American Cyanamid Company Process for the preparation of substituted and unsubstituted-2,3-pyridinedicarboxylates from chloromaleate or chlorofumarate or mixtures thereof
US5225560A (en) * 1990-06-15 1993-07-06 American Cyanamid Company Process for the preparation of dialkyl pyridine-2,3-dicarboxylate and derivatives thereof from dialkyl dichlorosuccinate
US5124458A (en) * 1990-06-15 1992-06-23 American Cyanamid Company Process for the preparation of dialkyl pyridine-2,3-dicarboxylate and derivatives thereof from dialkyl dichlorosuccinate
US5122608A (en) * 1990-12-19 1992-06-16 American Cyanamid Company Method for the preparation of substituted and unsubstituted 2,3-pyridine and quinolinedicarboxylic acids
US5281713A (en) * 1991-12-20 1994-01-25 American Cyanamid Company Process for the manufacture of 2-alkoxymethylacrolein
US5276157A (en) * 1991-12-20 1994-01-04 American Cyanamid Company Process for the purification of 2,3-pyridine and quinolinedicarboxylic acid diester compounds
US5177266A (en) * 1991-12-20 1993-01-05 American Cyanamid Company Proccess for the manufacture of 2-alkoxymethylacrolein
DE4343923A1 (de) * 1993-12-22 1995-06-29 Basf Ag Pyridin-2,3-dicarbonsäureimide, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
JPH11508918A (ja) * 1995-07-11 1999-08-03 レイリー・インダストリーズ・インコーポレーテッド キノリン塩基の製造方法
NZ314904A (en) * 1996-06-10 1998-06-26 American Cyanamid Co Preparation of a herbicidal [(5,6-dicarboxy-3-pyridyl)methyl]ammonium halide
US5892050A (en) * 1998-01-28 1999-04-06 American Cyanamid Company Process for the preparation of pyridine dicarboxylate derivatives
US5925764A (en) * 1998-06-15 1999-07-20 Wu; Wen-Xue Process and intermediated for the manufacture of pyridine-2, 3-dicarboxylate compounds
US6080867A (en) * 1998-06-15 2000-06-27 American Cyanamid Company Process and intermediates for the manufacture of pyridine-2,3-dicarboxylate compounds
US7795439B2 (en) * 2004-06-25 2010-09-14 Basf Aktiengesellschaft In-situ treatment of pyridine 2,3-dicarboxylic acid esters with an oxidizing agent
CN103373958B (zh) * 2012-04-18 2015-11-04 中国中化股份有限公司 5-乙基吡啶-2,3-二甲酸二乙酯的制备方法
EP3782985A1 (fr) 2019-08-19 2021-02-24 BASF Agrochemical Products B.V. Procédé de fabrication de dérivés d'acide 5-méthoxyméthylpyridine-2,3-dicarboxylique
CN115403518A (zh) * 2022-09-19 2022-11-29 浙江伟锋药业有限公司 一种5-烷基吡啶-2,3-二羧酸酯的连续流合成工艺

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4460776A (en) * 1982-05-25 1984-07-17 American Cyanamid Company Process for the preparation of 6-substituted-2,3-pyridinedicarboxylic acid diesters
EP0127883A2 (fr) * 1983-06-02 1984-12-12 American Cyanamid Company (2-Imidazolin-2-yl)thiéno- et furo (2,3-b) et (3,2-b) pyridines et intermédiaires pour sa préparation et leur utilisation comme agents herbicides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2453305A1 (de) * 1973-12-05 1975-06-12 Heyden Chem Fab Neue hydrazine, hydrazide und hydrazone von pyrazolo(3,4-b)pyridin-6-carbonsaeuren und -carbonsaeureestern und ihre salze
US4748244A (en) * 1984-05-11 1988-05-31 Ciba-Geigy Corporation Process for the preparation of pyridine-2-3-dicarboxylic acid derivatives, and novel 1-amino-1,4-dihydropyridine-2-3-diarboxylic acid derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4460776A (en) * 1982-05-25 1984-07-17 American Cyanamid Company Process for the preparation of 6-substituted-2,3-pyridinedicarboxylic acid diesters
EP0127883A2 (fr) * 1983-06-02 1984-12-12 American Cyanamid Company (2-Imidazolin-2-yl)thiéno- et furo (2,3-b) et (3,2-b) pyridines et intermédiaires pour sa préparation et leur utilisation comme agents herbicides

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE1003158A5 (fr) * 1986-03-10 1991-12-17 Shell Int Research Preparation de composes heterocycliques.
FR2595354A1 (fr) * 1986-03-10 1987-09-11 Shell Int Research Preparation de composes heterocycliques
US4973695A (en) * 1987-01-06 1990-11-27 Sugai Chemical Ind. Co., Ltd. Process for preparing pyridine-2,3-dicarboxylic acid compounds
EP0274379A2 (fr) * 1987-01-06 1988-07-13 Sugai Chemical Industry Co., Ltd. Procédé de préparation de dérivés d'acide pyridine-2,3-dicarboxylique
EP0274379A3 (en) * 1987-01-06 1989-09-06 Sugai Chemical Industry Co., Ltd. Process for preparing pyridine-2,3-dicarboxylic acid compounds
EP0357792A4 (en) * 1988-03-18 1990-09-05 Sugai Chemical Industry Co., Ltd. Process for preparing pyridine-2,3-dicarboxylic acid compounds
EP0357792A1 (fr) * 1988-03-18 1990-03-14 Sugai Chemical Industry Co., Ltd. Procede de preparation de composes de l'acide pyridine-2,3-dicarboxylique
US5175300A (en) * 1988-03-18 1992-12-29 Sugai Chemical Ind. Co., Ltd. Process for preparing pyridine-2,3-dicarboxylic acid compounds
EP0588372A1 (fr) * 1988-03-18 1994-03-23 Sugai Chemical Industry Co., Ltd. Procédé de préparation de composés de l'acide pyridine-2,3-dicarboxylique
EP0415767A2 (fr) * 1989-08-31 1991-03-06 Hoechst Celanese Corporation Procédé pour la préparation de dérivés d'acide pyridine-carboxylique
EP0415767A3 (en) * 1989-08-31 1991-09-04 Hoechst Celanese Corporation Process for preparing pyridine carboxylic acid derivatives
TR24836A (tr) * 1989-08-31 1992-05-01 Hoechst Celanese Corparation PIRIDIN KARBOKSILIK ASIT TüREVLERININ HAZIRLANMASI ICIN PROSES
EP0461401A1 (fr) * 1990-06-15 1991-12-18 American Cyanamid Company Procédé pour la préparation des esters dialcoyliques 2,3-dicarboxy-pyridine et leurs dérivés à partir des esters dichloromaléiques
EP0564083A1 (fr) * 1992-03-30 1993-10-06 Hoechst Celanese Corporation Conversion d'esters d'acide pyridine-2,3-dicarboxyliques en leur anhydrides cycliques
DE102005022043B3 (de) * 2005-05-09 2006-09-28 MAE Maschinen- und Apparatebau Götzen GmbH & Co. KG Verfahren und Vorrichtung zum Richten eines länglichen Werkstückes
US8161289B2 (en) 2005-12-21 2012-04-17 SanDisk Technologies, Inc. Voice controlled portable memory storage device

Also Published As

Publication number Publication date
IL80284A0 (en) 1987-01-30
DK512586A (da) 1987-04-29
ZA868167B (en) 1987-06-24
CA1274831A (fr) 1990-10-02
KR870003989A (ko) 1987-05-06
JPS62106081A (ja) 1987-05-16
DK512586D0 (da) 1986-10-27
ES2000910A6 (es) 1988-03-16
ATE60758T1 (de) 1991-02-15
IE862605L (en) 1987-04-28
DD254000A5 (de) 1988-02-10
HUT44016A (en) 1988-01-28
DK163505B (da) 1992-03-09
AU6441586A (en) 1987-04-30
DE3634975C2 (de) 1997-12-18
IL80284A (en) 1990-07-26
KR940001774B1 (ko) 1994-03-05
EP0220518A3 (en) 1988-03-30
CS259894B2 (en) 1988-11-15
IE59324B1 (en) 1994-02-09
BR8605210A (pt) 1987-07-28
DE3634975A1 (de) 1987-04-30
JPH0768216B2 (ja) 1995-07-26
DK163505C (da) 1992-08-24
HU198909B (en) 1989-12-28
AR241244A1 (es) 1992-03-31
EP0220518B1 (fr) 1991-02-06
US4723011A (en) 1988-02-02
AU592379B2 (en) 1990-01-11

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